The instant invention relates to 2-n-pentyl-2-cyclohexen-1-one having the structure: ##STR2## and uses thereof in augmenting or enhancing the aroma of consumable materials.
Materials which can provide muguet, orange, coconut, lactonic and jasmine-like aroma nuances are well known in the art of perfumery. Many of the natural substances which provide such fragrances and contribute the desired nuances to perfumery compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
The compound having the structure: ##STR3## the 2-n-pentyl-2-cyclohexen-1-one of our invention, is shown to be useful as a synthesis intermediate in preparing esters useful in perfumery having the structure: ##STR4## in U.S. Pat. No. 4,310,701 issued on Jan. 12, 1982, the specification for which is incorporated by reference herein.
Arctander "Perfume and Flavor Chemicals (Aroma Chemicals) II" at monograph 2457 describes a possible precursor of the 2-n-pentyl-2-cyclohexen-1-one of our invention having the structure: ##STR5## which precursor is 2-n-pentylidene-cyclohexanone-1 having the structure: ##STR6## Arctander states that this compound is warm and slightly spicy, having a jasmine odor of excellent tenacity. Arctander further states that this compound is "less floral than the most popular iso-Jasmones . . . "
Arctander "Perfume and Flavor Chemicals (Aroma Chemicals)" Vol. I at monograph 1789 describes "iso-Jasmone" as follows:
"Commercial products under this name are mixtures of several isomer ketones of which: PA0 The literature has been very illogical and inconsistent on the subject of nomenclature, identity and odor description of the commercially available iso-Jasmones, etc. PA0 One of the main points of disagreement seems to be the preference of isomer (2) as compared to one or more of the isomers which have an unsaturated ring and a saturated side chain. PA0 Yet, it has also been claimed that the hydrogenated product (which may be identical even when prepared from two different unsaturated isomers) has a superior odor. PA0 The author finds that personal opinions on the odor of these materials will not contribute constructively to the problem, and only general odor descriptions are therefore listed. PA0 "iso-Jasmone" is a name given to commercial products of very widely different composition. The fact that there are several "price-levels" also emphasize the difference in opinion as to which odor is closest to that of natural Jasmone, and which is the most desirable for general perfumery use. PA0 Although iso-Jasmone is quoted in literature with a chemical structure formula, commercial products are components, some iso-Jasmones have more than four major components. PA0 Iso-Jasmones are used widely in perfumes and flavors, and the very attractive cost of certain isomer blends has contributed to an extensive use of these ketones in quite ordinary perfumes, not just reserved for the finest or most costly compositions. PA0 Various effects can be achieved with various types of iso-Jasmone: floral, fruity, minty, warm, diffusive, "lifting", oily, ets. but with respect to Jasmine similarity, they are all inferior to cis-Jasmone . . . " PA0 (a) Mixing a first amount of a liquid polyolefin, e.g., polyethylene or polypropylene with a relatively large amount of scent imparting material (in this case the 2-n-pentyl-2-cyclohexen-1-one of our invention) to form a flowable mass; PA0 (b) Forming drops of said mass and causing substantially instantaneous solidification of said drops into polyolefin pellets having a relatively large amount of such scent imparting materials as the 2-n-pentyl-2-cyclohexen-1-one of our invention imprisoned therein; PA0 (c) Melting the pellets with a second amount of said polyolefin said second amount being larger than said first amount; and PA0 (d) Solidifying the melt of (c).
(1) n-Hexyl-cyclopenten-2-one: is described under DIHYDRO-iso-JASMONE. No. 955. PA1 (2) n-Hexylidene cyclopentanone: is described under alpha-HEXYLIDENE CYCLOPENTANONE. No. 1670. PA1 (3) 1-n-HEXYL-2-CYCLOPENTEN-1-ONE, so-called Dihydrojasmone. No. 1659.
At monograph 1659, Arctander describes for use in perfumery 2-n-hexyl-2-cyclopenten-1-one having the structure: ##STR7## as "Powerful fruity-green, oily and somewhat floral odor of moderate tenacity."
Nothing in the prior art, however, expressly or implicity states the unexpected, unobvious and advantageous perfumery properties of the 2-n-pentyl-2-cyclohexen-1-one having the structure: ##STR8##